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This study examines the intraday and overnight performance of S&P 500 exchange traded fund (SPY) put options from May 2005 through April 2010. The basic findings indicate that deviations of put option price changes from projections based on Black–Scholes–Merton (BSM) deltas are often substantial and can be explained mostly by the negative relation between implied volatility and SPY returns. The study then examines the impact of adjusting deltas with out of sample estimates of the relationship between implied volatility and SPY returns on the profitability of intraday and overnight delta hedged short SPY put option positions. The findings indicate that these adjustments lower P&L volatility and improve measures of downside risk relative to both BSM deltas and deltas adjusted with the volatility skew. © 2012 Wiley Periodicals, Inc. Jrl Fut Mark 33:443-468, 2013